Research progress of visible-light-responsive dye-based multi-functional photoinitiating systems

doi:10.16085/j.issn.1000-6613.2023-0197

Abstract

Abstract:

Dyes have aroused great research interest in the photocuring field due to their excellent photochemical and photophysical properties. The introduction of dyes into traditional photoinitiating systems can not only improve the visible-light absorption abilities for the systems, but also effectively facilitate the rate of photoinitiated polymerization. The dye-based multi-functional photoinitiating systems can successfully initiate many free radical polymerizations of acrylates and cationic polymerizations of epoxides under visible-light source, and they also show a broad application prospect in the fields of efficient preparation of materials and photocuring 3D printing. Based on these, this literature summarized the working mechanisms of dyes serving as photosensitizers, and reviewed the research progress of the different types of dyes in visible-light initiating systems in recent years. Furthermore, the future development of visible light day-based photosensitizers in this direction were prospected. Also, the importance of introducing dyes into visible light initiation system was emphasized directly, aiming at promoting the development of material preparation towards a more energy saving and environment protection direction, and providing new ideas for the future design and development of visible-light initiating systems.

Key words: dyes, photosensitizers, visible light, photoinitiating systems, photopolymerizations

摘要：

染料由于其优异的光化学和光物理性质引起了光固化领域极大的研究兴趣。将染料引入传统的光引发体系不仅可以提高体系对可见光的吸收能力，还能有效提高光引发聚合反应速率。在可见光源下，染料基多功能光引发体系不但可以成功引发多种丙烯酸酯的自由基聚合反应和环氧化物的阳离子聚合反应，同时在材料高效制备和光固化型3D打印等方面也显示出广阔的应用前景。基于此，本文总结了染料作为光敏剂的作用机理，综述了近年来不同类型的染料在可见光引发体系中的研究进展，对未来可见光染料基光敏剂的进一步发展进行了展望，并强调将染料直接引入可见光引发体系的重要意义，旨在促进材料制备向着更加节能、环保的方向发展，为可见光引发体系的未来设计和发展提供新思路。

关键词: 染料, 光敏剂, 可见光, 光引发体系, 光聚合反应

CLC Number:

TQ311

ZHOU Ying, HAO Kang'an, WANG Shaofan, HUANG Anrong, WU Chong, ZUO Xiaoling. Research progress of visible-light-responsive dye-based multi-functional photoinitiating systems[J]. Chemical Industry and Engineering Progress, 2023, 42(12): 6438-6451.

周颖, 郝康安, 王少凡, 黄安荣, 吴翀, 左晓玲. 可见光响应型染料基多功能光引发体系的研究进展[J]. 化工进展, 2023, 42(12): 6438-6451.

Figures/Tables 11

References 88

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染料	光吸收性能	适用的辐照光源	光聚合类型	单体类型及其转化率	颜色	参考文献
CCM (CCM/Iod/TPP PIS)	ε_417nm约58500L/(mol·cm)	Lamp 407nm/Sunlight LED bulbs 392nm 455nm 518nm	自由基/阳离子光聚合反应	Bis-GMA/TEGDMA （300s；71%）	黄色	[44]
14-DHAQ (14-DHAQ/Iod/NVK PIS) (14-DHAQ/TEAOH/R-Br PIS)	ε_455nm约7000L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；50%)，EPOX (800s；67%)	多色	[45]
15-DHAQ (15-DHAQ/Iod/NVK PIS) (15-DHAQ/TEAOH/R-Br PIS)	ε_455nm约3500L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；42%)，EPOX (800s；15%)	多色	[45]
18-DHAQ (18-DHAQ/Iod/NVK PIS) (18-DHAQ/TEAOH/R-Br PIS)	ε_455nm约3900L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；55%)，EPOX (800s；79%)	多色	[45]
ECMO (ECMO/THS PIS)	ε_405nm约11800L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	HDDA (300s；64%)	黄色	[46]
3HF-S (3HF-S/TEOA PIS)	ε_405nm约17448L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	TPGDA (180s；80%)	黄色	[47]
3HF-C (3HF-C/TEOA PIS)	ε_405nm约16071L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	TPGDA (180s；20%)	黄色	[47]
3HF-F (3HF-F/TEOA PIS)	—	LED bulb (405nm)	自由基/阳离子光聚合反应	PEGDA (300s；82%)	黄色	[48]
CA-ID-4 (CA-ID-4/MDEA PIS)	ε_535nm约72000L/(mol·cm)	LED bulb (525nm)	自由基/阳离子光聚合反应	HDDA (30min；74.2%)	红色	[49]
CI-2 (CI-2/MDEA PIS)	ε_510nm约11738L/(mol·cm)	LED bulb (455nm)	自由基/阳离子光聚合反应	HDDA (30min；86%)	红色	[50]
DCJTB (DCJTB/Iod PIS) (DCJTB/Iod/NVK PIS) (DCJTB/MDEA/R′-Cl PIS)	ε_501nm约51100L/(mol·cm)	Laser diode (532nm) halogen lamp	自由基/阳离子光聚合反应	EPOX (DCJTB/Iod/NVK PIS；800s；66%)	红色	[51]
h-B3FL (h-B3FL/Iod PIS) (h-B3FL/Iod/NVK PIS) (h-B3FL/MDEA/R′-Cl PIS)	ε_484nm约18300L/(mol·cm)	Laser diode (532nm) halogen lamp	自由基/阳离子光聚合反应	EPOX (h-B3FL/Iod/NVK PIS:800s；33%))	红色	[51]
OB28 (OB28/Iod PIS)	ε_400nm约13400L/(mol·cm)	LED@420nm	自由基光聚合反应	TMPTA (600s；42%)	白色	[52]
QTXP (QTXP/NVK/Iod PIS)	ε_443nm约8000L/(mol·cm)	halogen lamp laser diode (457nm) LED@462nm	自由基/阳离子光聚合反应	EPOX (457nm：800s；62%)	无色	[53]
PQTXP (PQTXP/NVK/Iod PIS)	—	halogen lamp laser diode (457nm)	自由基/阳离子光聚合反应	EPOX (457nm：800s；48%)	无色	[53]
A₃ (A3/Iod/EDB PIS)	ε_330nm约33000L/(mol·cm)	LED@405nm LED@455nm	阳离子光聚合反应	EPOX (405nm：800s；55%； 455nm：800s；54%)	无色	[54]

染料	光吸收性能	适用的辐照光源	光聚合类型	单体类型及其转化率	颜色	参考文献
CCM (CCM/Iod/TPP PIS)	ε_417nm约58500L/(mol·cm)	Lamp 407nm/Sunlight LED bulbs 392nm 455nm 518nm	自由基/阳离子光聚合反应	Bis-GMA/TEGDMA （300s；71%）	黄色	[44]
14-DHAQ (14-DHAQ/Iod/NVK PIS) (14-DHAQ/TEAOH/R-Br PIS)	ε_455nm约7000L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；50%)，EPOX (800s；67%)	多色	[45]
15-DHAQ (15-DHAQ/Iod/NVK PIS) (15-DHAQ/TEAOH/R-Br PIS)	ε_455nm约3500L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；42%)，EPOX (800s；15%)	多色	[45]
18-DHAQ (18-DHAQ/Iod/NVK PIS) (18-DHAQ/TEAOH/R-Br PIS)	ε_455nm约3900L/(mol·cm)	LED 455nm	自由基/阳离子光聚合反应	Bis-GMA and TEGDMA (300s；55%)，EPOX (800s；79%)	多色	[45]
ECMO (ECMO/THS PIS)	ε_405nm约11800L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	HDDA (300s；64%)	黄色	[46]
3HF-S (3HF-S/TEOA PIS)	ε_405nm约17448L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	TPGDA (180s；80%)	黄色	[47]
3HF-C (3HF-C/TEOA PIS)	ε_405nm约16071L/(mol·cm)	LED bulb (405nm)	自由基/阳离子光聚合反应	TPGDA (180s；20%)	黄色	[47]
3HF-F (3HF-F/TEOA PIS)	—	LED bulb (405nm)	自由基/阳离子光聚合反应	PEGDA (300s；82%)	黄色	[48]
CA-ID-4 (CA-ID-4/MDEA PIS)	ε_535nm约72000L/(mol·cm)	LED bulb (525nm)	自由基/阳离子光聚合反应	HDDA (30min；74.2%)	红色	[49]
CI-2 (CI-2/MDEA PIS)	ε_510nm约11738L/(mol·cm)	LED bulb (455nm)	自由基/阳离子光聚合反应	HDDA (30min；86%)	红色	[50]
DCJTB (DCJTB/Iod PIS) (DCJTB/Iod/NVK PIS) (DCJTB/MDEA/R′-Cl PIS)	ε_501nm约51100L/(mol·cm)	Laser diode (532nm) halogen lamp	自由基/阳离子光聚合反应	EPOX (DCJTB/Iod/NVK PIS；800s；66%)	红色	[51]
h-B3FL (h-B3FL/Iod PIS) (h-B3FL/Iod/NVK PIS) (h-B3FL/MDEA/R′-Cl PIS)	ε_484nm约18300L/(mol·cm)	Laser diode (532nm) halogen lamp	自由基/阳离子光聚合反应	EPOX (h-B3FL/Iod/NVK PIS:800s；33%))	红色	[51]
OB28 (OB28/Iod PIS)	ε_400nm约13400L/(mol·cm)	LED@420nm	自由基光聚合反应	TMPTA (600s；42%)	白色	[52]
QTXP (QTXP/NVK/Iod PIS)	ε_443nm约8000L/(mol·cm)	halogen lamp laser diode (457nm) LED@462nm	自由基/阳离子光聚合反应	EPOX (457nm：800s；62%)	无色	[53]
PQTXP (PQTXP/NVK/Iod PIS)	—	halogen lamp laser diode (457nm)	自由基/阳离子光聚合反应	EPOX (457nm：800s；48%)	无色	[53]
A₃ (A3/Iod/EDB PIS)	ε_330nm约33000L/(mol·cm)	LED@405nm LED@455nm	阳离子光聚合反应	EPOX (405nm：800s；55%； 455nm：800s；54%)	无色	[54]

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